Helvetica Chimica Acta p. 237 - 261 (1987)
Update date:2022-08-04
Topics:
Seebach, Dieter
Juaristi, Eusebio
Miller, David D.
Schickli, Christof
Weber, Theodor
Chiral enolates of imidazolidinones and oxazolidinones from the title amino acids react with carbonyl compounds to afford the corresponding alcohols in excellent yields (see Scheme 5).Furthermore, the addition to aldehydes proceeds with high diastereoselectivity to give, after acid hydrolysis, threo-α-amino-β-hydroxy acids of high enantiomeric purity.Some of the threo-α-amino-β-hydroxy acids prepared in this work are the proteinogenic (S)-threonine (26), the naturally occuring (S)-3-phenylserine (28), and (S)-3-hydroxyleucine (27) as well as the unnatural (S)-4,4,4-rtifluorothreonine (30) and (S)-3-(4-pyridyl)serine (31).The N-methylamide of (2S,3R,4R,6E)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoic acid (32), the uniqe amino acid in the immunosuppressive cyclosporine, was prepared by the new method.This report presents also information suggesting that both steric and stereoelectronic effects are responsible for the good stereoselectivities observed.
View MoreBeijing Mashi Fine Chemical Co.,Ltd.
Contact:+86-10-61271592
Address:Room 506, Section B, Kaichi Mansion, Industrial Development
Junkai (Tianjin) Chemical Co., Ltd.
website:http://www.junkaichem.com
Contact:86-22-85689515
Address:Room 8-501, Building K2, The Hi-Tech Green Industrial Base, No.6, 6th Road, Hi-Tech Development Road, Tianjin Hi-Tech IndustrialPark, Tianjin, China.
SHANXI JINJIN CHEMICAL INDUSTRIAL CO.,LTD
website:http://www.jinjingroup.com
Contact:4009982989
Address:Economic And Technological Development Zone,Hejin?City,Shanxi Province?,China
CHANGZHOU HANGYU PHARMACEUTICAL TECHNOLOGY CO., LTD
website:http://www.czyys.com
Contact:0086-519-88802789
Address:No.300,Yanling Middle Road, Changzhou, Jiangsu, China
Shandong LuZhou Amino Acid Co., Ltd
Contact:86-539-2218025
Address:yishui economic and technical development zone zhenxing south road
Doi:10.1021/jo01052a075
(1962)Doi:10.1002/adsc.201300211
(2013)Doi:10.3390/molecules23051154
(2018)Doi:10.1039/b717556f
(2008)Doi:10.1021/ja800738d
(2008)Doi:10.1016/j.poly.2007.11.020
(2008)